Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions

Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at the meta-position utilizing the inexpensive and safe bromine salts at room...

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Veröffentlicht in:Journal of organic chemistry 2021-11, Vol.86 (22), p.16144-16150
Hauptverfasser: Wu, Yanwei, Xu, Shanghui, Wang, Hong, Shao, Dongxu, Qi, Qiqi, Lu, Yi, Ma, Li, Zhou, Jianhua, Hu, Wei, Gao, Wei, Chen, Jianbin
Format: Artikel
Sprache:eng
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Zusammenfassung:Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at the meta-position utilizing the inexpensive and safe bromine salts at room temperature. A variety of brominated pyridine derivatives were obtained in 28–95% yields, and the reaction could be readily performed at a gram scale. By combining the installation and removing the directing group, the concept of meta-bromination of pyridines could be verified.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00923